


Matchmaker, Matchmaker, Find Me a Match

by thelonelywriter



Category: Supernatural
Genre: Alternate Universe - Teachers, First Kiss, M/M, Matchmaking, Mutual Pining
Language: English
Status: Completed
Published: 2015-06-17
Updated: 2015-06-17
Packaged: 2018-04-04 19:29:14
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,725
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/4150029
Author URL: https://archiveofourown.org/users/thelonelywriter/pseuds/thelonelywriter
Summary: <blockquote class="userstuff">
              <p>"Charlie, are you once again trying to spread your homosexual matchmaking unto unsuspecting victims?" he asked jokingly. Charlie rolled her eyes, giving him a light kick under the table.<br/>"Who are we trying to get together?" Ed asked through a mouthful of burger.<br/>"Mr. Novak and Mr. Winchester," Kevin said coolly, picking at his salad. Harry and Ed simultaneously groaned.<br/>"That's going to be a difficult one," Ed said, shaking his head. "I mean, have you seen those two in the hallways?"<br/>"Oh my God, I know right? Mr. Novak stares at him like he's the only thing that exists. Classic heart eyes," Charlie replied with exuberance.</p>
            </blockquote>





	Matchmaker, Matchmaker, Find Me a Match

**Author's Note:**

  * For [SlitheredFromEden](https://archiveofourown.org/users/SlitheredFromEden/gifts).



> This is a sort of prequel to a story that you can read [right here](http://archiveofourown.org/works/4142529) I haven't really written anything quite like this before so let me know what you think!

Charlie Bradbury happily pulled out her headphones as she sat down at the lunch table. "Don't you think Mr. Novak and Mr. Winchester would make, like, an amazing couple," she offered immediately to the students she sat with in the crowded lunch room. She had been thinking of it all day and she wanted to see what her friends would have to say, if they had noticed what she had. Jo looked taken aback whereas Kevin simply shrugged in indifference.

"Mr. Winchester? Charlie, he's as straight as they come," Jo said, raising her eyebrows. Kevin huffed a little breath of laughter, putting down his fork.

"I wouldn't necessarily say _straight_ more like, I dunno, bi," Kevin commented. Charlie pointed a finger at him.

"Exactly," she said. Jo shifted in her seat, putting her elbows on the table.

"What caused this sudden epiphany anyways?" Jo asked curiously. Charlie sighed.

"Well, I think a few weeks ago I actually picked up on how they act around each other and I swear they look like nervous teenagers guys, seriously," she explained with a knowing look.

Harry finally pulled himself out of the conversation he was having with Ed, listening vaguely to the excited words of Charlie. "Charlie, are you once again trying to spread your homosexual matchmaking unto unsuspecting victims?" he asked jokingly. Charlie rolled her eyes, giving him a light kick under the table. 

"Who are we trying to get together?" Ed asked through a mouthful of burger.

"Mr. Novak and Mr. Winchester," Kevin said coolly, picking at his salad. Harry and Ed simultaneously groaned.

"That's going to be a difficult one," Ed said, shaking his head. "I mean, have you seen those two in the hallways?" 

"Oh my God, I know right? Mr. Novak stares at him like he's the only thing that exists. Classic heart eyes," Charlie replied with exuberance.

"That's actually very true," Kevin said with a small smile. "And Mr. Winchester always trips or blushes when he sees Mr. Novak doing it and then Mr. Novak tries to cover up the fact that he was staring. Charlie's right, they are like two nervous teenagers," Kevin declared.

"I'm still a bit ambivalent about this," Jo butted in, eyes darting between Kevin and Charlie. "I mean, really? Mr. Winchester? With Mr. Novak? I'm not so sure," she trailed off. Harry rolled his eyes.

"Jo, we all know that you're ambivalent about this because you have the hots for Mr. Winchester," Harry told her in a matter of fact tone. Jo gave him a harsh kick under the table. "Ow! Someone throw a red flag down, Jo needs a penalty for excessive kicking," he grumbled.

"Look, I'm just saying that you should give it a chance, stay after a bit after your History class and then tomorrow we'll regroup," Charlie suggested to Jo.

"Oh God, does this mean that lunch will now become a discussion about the matchmaking of Mr. Winchester and Mr. Novak?" Harry groaned.

"At least until we get them together," Charlie replied with a mischievous grin, waggling her eyebrows.

\---

Jo hesitantly stayed behind a bit after her History class, sneaking around to the outside of the classroom. Dean was leaving his classroom to grab a drink of water from the breakroom, so he didn't even notice Jo standing outside of the door. Castiel's classroom was right across from Dean's, so it wasn't a surprise that the two ended up walking into each other when Castiel left his classroom at the exact same time. "Oh, shit, sorry Castiel, I was just um, just, getting a drink. From the breakroom. Water, that's uh, yeah, what I was getting," Dean spluttered out. Jo had to bite her lip to keep from laughing at the way Dean stumbled a bit as he backed away, rubbing his neck and blushing furiously.

"Oh, no it's fine, Cas, I mean Dean, you can call me Cas, you don't have to call me Castiel, not unless you, you know, want to, uhm, I should probably," Castiel said, his words messy, especially for an English teacher, as he backed away, pointing over his shoulder to his classroom.

"Yeah, yeah you um, do that Cas," Dean said, shooting him a nervous smile before they both disappeared in the opposite direction. 

Jo did have to admit that she had a crush on her teacher, on Dean, but when she saw the way that they had acted like that, the way they got so flustered and got stuck on their words, she started to reconsider Charlie's words. Maybe Charlie was right, maybe they were a little lovestruck.

\---

"Okay, fine, Charlie, you were right, they would make a cute couple," Jo grumbled as she sat down across from Charlie the next day. Charlie beamed back at her.

"Alright, so who's on board with the fact that Mr. Winchester and Mr. Novak are secretly in love?" Charlie asked, receiving nods from around the table. 

"You know she actually just asked who would help in her scheme of getting them together," Harry whispered to Ed. Charlie turned and shot Harry a look.

"I can hear you Harry," she said before turning back to face Jo. "Alright, so what's our plan of action?" Charlie questioned, her eyes sweeping those who sat in front of her. Everyone just exchanged unknowing glances, a few shrugs circling their way around. Charlie groaned. "C'mon guys, we need something," she told them urgently.

"I say we talk to Claire," Kevin suggested. "Mr. Novak is her uncle, maybe she knows if he's taken or not."

"I like how you think Kevin," Charlie declared, immediately getting out of her seat to call Claire over to their table.

Claire, who sat a table or two away, got up from her seat, walking over to sit next to Charlie. "Tell me about your uncle," Charlie demanded, staring intently at Claire. 

"Cas? Uhm, well there's not too much to tell. I see him every once in a while at family gatherings or sometimes he comes over for dinner. Why?" Then Claire's eyes widened and she groaned. "Please don't tell me you have a crush on him, I've already been through that with Meg," she muttered, shaking her head.

"What? No, oh my God no," Charlie clarified. "But... is he taken?" Claire gave her a strange look.

"No, he's single. What is this about, anyways?" Claire asked impatiently.

"Well, it's just that we've noticed some, ahem, certain forms of behavior between your uncle and Mr. Winchester," Ed spoke up. Claire paused, then laughed.

"Oh, okay," she said, still chuckling. "Charlie must be trying to get them together, right?" she asked. 

"What? Psshhh, noo," Charlie lied. Kevin rolled his eyes, picking up a french fry.

"Charlie is an awful liar," he commented and Charlie let out an aggravated sigh.

"Alright, alright, fine," Charlie grumbled. Claire leaned on the table, looking at Charlie.

"I shouldn't be telling you any of this, but I would love to see Cas and Mr. Winchester together. Cas is kind of lonely, but he doesn't let it show. And he would _definitely_ like to get Mr. Winchester alone. He hasn't said anything but I have Mr. Winchester for History and every time I see Cas at dinner or at some family event he _always_ asks how History is going. Not Math, not English, which is what he actually teaches, but History and of course he tries to pretend like he's not secretly asking if Mr. Winchester has confessed his love for him yet, but he is, like Charlie, a bad liar and he's awful at covering things up. And Mr. Winchester kind of always acts a little... off when he calls on me, like he's saying the name, 'Novak,' for the first time." Everyone sat for a moment, absorbing the information Claire had just spilled. It only made Charlie even more determined.

"Claire, with your extensive knowledge of Mr. Novak, would you care to join our special ops mission of trying to get him together with Mr. Winchester?" Charlie asked kindly.

Claire thought for a moment. She knew that Cas had liked Mr. Winchester for a while, and she also knew that Cas was a little lonely and she hated to see him like that. And though she wasn't supposed to be giving out private information about her uncle to other students, but she knew that if her and her other friends didn't make a move for Cas or Mr. Winchester, they would likely never get together. "Okay, fine," she agreed to Charlie's great pleasure. "Do you guys have like secret meetings in the janitor's closet or something? Should I R.S.V.P?" she joked.

"Nah, we just talk about it during lunch," Harry responded and Claire nodded, chuckling a little.

"Sounds like a plan. I'm excited to see what Charlie has brewing in her mind," Claire told them.

\---

The next day the group all sat together at the table, Claire an exciting new add-on. "We could lock them in one of their classrooms," Harry suggested.

"Oh my God, no, we don't want teacher on teacher porno material just yet," Charlie commented making Claire wrinkle her nose.

"Gross, Charlie, that's my uncle your talking about," she said, giving Charlie a light shove.

"What about writing a note and leaving it on one of their desk's? Like a love note or something," Kevin suggested.

"Nah," Charlie said, shaking her head. "I think that should be our last resort. That's a little sneaky, plus Mr. Novak is shy so he'd likely end up backing out or they would get confused and it could end in pure angst," she finished. 

"We need to start off slow, Cas is a little nervous so it's not like they'd be confessing their passionate feelings and their deep need to get in each other's pants. We need to build upon the awkward tension between them," Claire contemplated.

"Yeah, but how do we do that?" Ed asked.

"What about the accidental kiss method," Jo suggested. "We could bump into them so that they bump into each other and then their lips could meet and boom, amour."

"Yeah but that's a gamble," Ed said, a distasteful look on his face. "They could just end up smacking foreheads or getting nosebleeds."

"Well, it all depends on our placement and the velocity of force we use to push them together," Kevin explained calmly. Charlie just gave him a look and Kevin sighed. "I've been studying for my Physics test, okay?" 

Charlie thought about what Jo and Kevin had said, thinking that though it was a gamble it may be worth it. Either way they were going to bump into each other and even if they got nosebleeds or wounds they could nurse them together. It was bonding, so why not take a chance with it. "I say we do it," Charlie said. The rest of the group looked at her skeptically, but she reassured them. "Don't worry, I have a plan."

\---

Charlie, Claire, and Jo stood in the almost empty hallways that were still partially filled with straggling students. Class had just ended, so people were wandering about. Jo stood by the lockers, her job to watch the event and give a play by play afterwards. Meanwhile Charlie stood near Dean's doorway, ready to pounce and begin her job of distracting Dean. Then Claire was outside of Castiel's classroom, standing calmly and waiting to pelt Cas with questions. They all looked around, giving an affirmative nod, and the plan was put into action.

Castiel was standing by the doorway when he saw Claire and smiled. "Claire, how are you?" Claire smiled that smile that she knew melted Castiel's heart and thus began the sweet talking.

"I'm good Uncle Cas, I just wanted to come and ask you a few questions," she said, slowly drawing him out of the classroom.

At the same time Charlie did the same, managing to get Dean out of the classroom. "Mr. Winchester, hey, just who I was looking for!" she said with a smile. 

"Hey Charlie," Dean responded. "What's up?" he asked.

"Oh, well I was just wondering if you could tell me anything about what it's like to be a teacher. I think teaching is great and I think I'd love to teach once I graduate from college," she said sweetly. She could tell that the question caught Dean off guard. It was a strange question after all. But she slowly did the same thing Claire had done, moving him out of the classroom so that he was turned towards her, his back facing Cas' classroom and Cas himself.

Claire took slow steps forward so that Castiel had to move backwards, pelting him with questions, enough so that he was distracted enough to not hear Dean and to not realize he was slowly walking backwards. Charlie did the same, guiding Dean backwards, closer and closer to Cas. 

Both Cas and Dean were equally caught off guard and distracted, not realizing what exactly was going on, only listening to the fast speech of Charlie and Claire and the muffled noises of the students in the hallways. 

Right as Cas and Dean were nearly back to back, Charlie and Claire looked over to Jo who gave them the signal to move the plan into step two. "Oh, look out behind you!" Claire and Charlie said at the same time. Dean and Cas turned around, met with the sight of each other. Before either of them could blink Claire "tripped," falling forwards into Castiel, enough to give him a light shove towards Dean.

Castiel's hands flew out to keep him from falling, landing on Dean's shoulders as his face moved forward, completely on accident.

And if by miracle, their lips met, not softly and sweetly, but a little forcefully and off center. Immediately Claire and Charlie scurried away as Jo stood quietly at her post, watching the aftermath. Cas pulled back, his eyes the size of dinner plates, blushing furiously. Dean just gaped back at him, the two staring at each other, saying nothing at first. 

By now the hallways were clear, no one in them except Jo, Cas, and Dean. "Did that just happen?" Castiel asked quickly.

"I- I think it did," Dean spluttered out quietly.

"I'm um, I'm sorry I didn't mean to, Claire tripped and..." Castiel trailed off, looking into Dean's eyes. Neither of them had backed away, they were still just inches away from each other.

"No, no don't apologize, it's fine," Dean murmured back.

There was a pause where Jo was just about to walk away figuring that all the action was said and done with but then Dean was grabbing Castiel's shirt and pressing his lips down unto Cas' as if he had been starving for it. Castiel made a surprised noise that was muffled my Dean's mouth on his own before his hands came curiously back up to Dean's shoulders.

Jo had to cover her mouth to keep from screaming. Mr. Novak and Mr. Winchester were actually full out kissing, practically swapping saliva in the middle of the hallway. And oh my God was this actually happening? Her heart jumped at the thought of telling everyone tomorrow at lunch.

\---

"Oh my God, did they use tongue?" Charlie asked excitedly at Jo's news.

"Well, I was pretty far away so it was hard to tell but I bet they were," she replied smugly.

"I'm just glad that Cas won't have to mope around all the time now," Claire commented, crunching on a chip.

"God, and the longing angsty glances will finally subside," Kevin sighed in relief.

"I'm just glad this is over with so lunch isn't strategically discussed plots on getting them together," Harry said. 

"No, now it's just gonna be Charlie swooning over their hush-hush relationship," Jo said with a chuckle.

"Oh!" Charlie said, wiggling to sit up in her seat. "We need a ship name," she explained. Everyone groaned in response to her words. "Oh, c'mon, it's not that bad."

"Well, we should at least use their first names, their last names are too long," Kevin said to which Charlie agreed, nodding.

"Deancas? Or maybe Casdean?" she muttered under her breath. Then she found the perfect name and beamed up at the others. "Destiel, that's it. Dean Winchester and Castiel Novak, two idiots in love. Destiel."

**Author's Note:**

> Ta-da!! *jazz hands* I hope you liked it, and thank you so much for reading!! Feedback is great and if you wanna read the sequel the link is up top in those notes!!


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